Chapter 17: Aldehydes and Ketones. Nucleophilic Additionto C=O

Summary

Aldehydes (RCHO) and ketones (RCOR') are very important functional groups, characterised by the presence of an acyl group (C=O) bonded either to H (aldehydes) or another C (ketones).
There are two contrasting, but equally important reactivity patterns for these compounds:

1.  Aldehydes and ketones are attacked by nucleophiles due to the electrophilic character of the carbonyl C. (Chapter 17)
2.  Treatment of aldehydes and ketones with a suitable base can lead to the formation of a nucleophilic species called an enolate that reacts with electrophiles. (Chapter18)

In this chapter, we will be looking at the reactions of aldehydes andketones with nucleophiles:

• Nomenclature
• Physical Properties
• Structure
• Reactivity

• Overview
• Ozonolysis of Alkenes (review)
• Hydration of Alkynes (review)
• Oxidation of Alcohols (review)
• Friedel-Crafts Acylation of Aromatics (review)

• Nucleophilic Addition Reactions
• Relative Reactivity
• Overview of Reactions
• Reduction of Aldehydes and Ketones
• To Hydrocarbons
• Using Hydrides to give Alcohols
• Using Carbon Nucleophiles
• Formation of Cyanohydrins
• Reactions of Organometallic Reagents
• The Wittig Reaction
• Using Nitrogen Nucleophiles
• Primary Amines and Derivatives
• Secondary Amines to give Enamines
• Using Oxygen Nucleophiles
• Formation of Hydrates
• Alcohols to Acetals
• Oxidation Reactions
• Oxidation of Aldehydes
• Baeyer-Villager oxidation of Ketones

Problems

• Sample Problems
• More practice problems ?
• Reaction Drills

© Dr. Ian Hunt, Department of Chemistry